Synthesis and kinetic characterisation of omega-guanidinocarbonic acid ethyl esters as trypsin substrates.
Aliphatic omega-guanidinocarbonic acid ethyl esters of different chain length (C3-C6) were synthesized and characterized as 4-toluenesulfonates. The kinetic parameters of the trypsin-catalyzed hydrolysis indicate that the ethyl ester of delta-guanidinovaleric acid is the most effective substrate in this series. The Km value of this compound is in the same order of magnitude as those of arginine-containing ester substrates like N alpha-benzoylarginine ethyl ester (BAEE). However, kcat is decreased by approximately two orders of magnitude.
Schuster
M
M
Department of Biochemistry, Karl Marx University, Leipzig.
Medvedkin
V N
VN
Schellenberger
V
V
Mitin YuV
Jakubke
H D
HD
D000600:Amino Acids, Dicarboxylic / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D001120:Arginine / Q000031:analogs & derivatives / Q000378:metabolism; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D006146:Guanidines / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D066298:In Vitro Techniques; D007700:Kinetics; D015394:Molecular Structure; D013379:Substrate Specificity; D014357:Trypsin / Q000378:metabolism*
D000600:Amino Acids, Dicarboxylic; D004952:Esters; D006146:Guanidines; D001120:Arginine; C009727:benzoylarginine ethyl ester; D014357:Trypsin